Hydroxyalkylpyridinethionamides



p 3,045, 24 Patented July 17, 1962 3,045,024 HYDROXYALKYLPYRIDINETHIONAMIDES Francis E. Cislak, Indianapolis, Ind., assignor to Reilly Tar & Chemical Corporation, Indianapolis, Ind., a corporation of Indiana No Drawing. Filed Feb. 3, 1961, Ser. No. 86,857

Claims. (Cl. 260-2943) This invention relates to new chemical compounds and to the process of making them. More particularly, it re- 10 lates to hydroxyalkylpyridine-thionamides having the following structural formula:

HO-R -NH,

Illustrative of the manner in which my invention may 7 be practiced, I cite the following examples:

EXAMPLE 1 4-HydroxypropyI-Z-Pyridin-Thionamide CHgCHzCHiOH 100 grams of Z-cyano-4-hydroxypropylpyridine is dissolved in 1,000 grams of 30% ammoniacal methanol. The resulting solution is saturated with dry H S at 25 C. and then permitted :to stand at room temperature for about two days. The 4-hydroxypropyl-Z-pyridine-thionamide formed during this time is recovered in any con venient manner. One way of recovering the pyridinethionamide is to evaporate the methanol under vacuum. 0 The 4-hydroxypropyl-2-pyridine-thionamide remaining is pure enough for most purposes. If a purer product is desired, the above obtained thionarnide may be dissolved in a suitable solvent, such as acetone, pyridine, etc., treated with decolorizing carbon and hot filtered, the filtrate cooled to about 25 C., and the pure 4-hydroxypropyl-Z-pyridinethionamide recovered from the cooled filtrate.

EXAMPLE 2 Z-Hydroxyethyl-4-Pyridine-Thi0namide i C-NH Q H2 C H2 0 H The procedure of Example 1 is repeated with the exception that Z-hydroxyethyl-4 cyanopyridine is used in place of the 2-cyano-4-hydroxypropylpyridine.

, V EXAMPLES 3-(Alpha-Hydroxyethyl)-5 Pyridine-Thionamide H C-CH 6H The procedure of Example 1 is repeated with the exception that 3-(alpha-hydroxyethyl)-5-cyanopyridine is used in place of the 2-cyano-4-hydroxypropylpyridine.'

EXAMPLE 4 3-Hydr0xymethyl-2-Pyridine-Thionamide CHzOH lC-NH: N

The procedure of Example 1 is repeated with the exception that 3hydroxymethyl-Z cyanopyridine is used in place of the 2-cyano-4-hydroxypropylpyridine.

' EXAMPLE 5 2-Hydroxyethyl-5-Ethyl-6-Pyridine-Thi0namide HzN-C CHaCHaOH The procedure of Example 1 is repeated with the exception that 2-hydroxyethyl-5-ethyl-6 cyanopyridine is used in place of the 2-cyano-4-hydroxypropylpyridine.

EXAMPLE 6 4 Gamma-H ydroxybutyl -2-Pyridin e-Thionamide (1)11 CHzCHr-CH-QH;

([?-NH, 7 s The procedure of Example 1 is repeated with the exception that 2-cyano-4-('gamma-hydroxybutyl)pyridine is used in place of the 2 cyano-4-hydroxypropylpyridine.

EXAMPLE 7 6-H ydroxyethyI-Z-Pyridine-Thionamide trolling the action of non-oxidizing inorganic acids upon metals. A 5% solution of my hydroxyalkylpyridine-thionamides in high boiling coal tar bases is particularly useful in inhibiting the action of dilute aqueous sulfuric acid upon steel.

HO-R Cr-NH:

wherein R is lower alkyl and R is selected from the group consisting of hydrogen and lower alkyl.

2. The compound 2-hydroxyethy1-4-pyridine-thionamide. 1 3. The compound 4-hydroxypropy1-2-pyridine-thionamide.

4. The compound 3-hydroxymethyl-2-pyridine-thion- :amide.

5. The compound 6-hydroxyethyl-Z-pyridine-thionamide.

6. The compound Z-hydroxyethyl-S-ethy1-6-pyridinethionamide.

References Cited in the file of this patent UNITED STATES PATENTS Lee Sept. 29, 1953 FOREIGN PATENTS 800,250 Great Britain Aug. 20, 1958 OTHER REFERENCES Whitmore: Organic Chemistry, 2nd Ed., page 415 (1951) (Van Nostrand). 

1. HYDROXYALKYLPYRIDINETHIONAMIDES HAVING THE FORMULA: 